


Don't Go Easy On Me

by BijutsuYoukai



Series: Devildom Tasks [5]
Category: Shall We Date?: Obey Me!
Genre: Bondage, Demon Sex, F/M, Kinktober Sequel, Oral Sex, Overstimulation, Plot What Plot/Porn Without Plot, Shameless Smut, Stomach Bulge, Vaginal Sex, slight size kink
Language: English
Status: Completed
Published: 2020-12-25
Updated: 2020-12-25
Packaged: 2021-03-10 23:41:43
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,595
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28095594
Author URL: https://archiveofourown.org/users/BijutsuYoukai/pseuds/BijutsuYoukai
Summary: In which Diavolo obliges reader’s request to not go easy on them regarding punishment for ogling his demon form.(Kinktober Sequel)
Relationships: Diavolo (Shall We Date?: Obey Me!)/Main Character, Diavolo (Shall We Date?: Obey Me!)/Reader
Series: Devildom Tasks [5]
Series URL: https://archiveofourown.org/series/1996582
Comments: 5
Kudos: 175





	Don't Go Easy On Me

**Author's Note:**

> So, as the summary and tags suggest, this is a sequel to one of my Kinktober chapters! (Specifically Sex Demon, which you can read [here](https://archiveofourown.org/works/26459062/chapters/65408527).). So here’s my first piece of actual smut with Diavolo rather than just teases ala Kinktober.
> 
> So without further ado, Happy Holidays, and please enjoy the demon lord dicking.

Several days had gone by since the night of the party and your mortifying moment of ogling the current ruler of the Devildom. Several days had passed since he caged you against a wall and kissed you and made you realize you wanted more. Several days had flown by and you found yourself distracted from school duties and the usual affairs of the House of Lamentation. If the seven brothers noticed the change in your behavior, they said nothing of it.

Trying to focus on classwork one evening - and not to recall the way Diavolo’s lips had molded to yours, so warm and fierce - the soft sound of an incoming message on your D.D.D. disrupted you further. Welcoming the brief respite from your scattered thoughts, you snatched up the device. But your heart thundered and your face flushed when you saw the name on the message. Lord Diavolo.

**Lord Diavolo X:XX PM:** Are you free this evening?

 **Lord Diavolo X:XX PM:** I’d like you to come visit me at the castle for the arrangement we talked about.

 **Lord Diavolo X:XX PM:** If that’s what you want still, that is.

The messages came in quick succession and your heart pounded faster, your breath sticking in your throat. You had remembered the feverish kiss often, but you hadn’t dared to recall the bold words you had spoken and how brazenly you acted. But there was the reminder staring at you from the illuminated screen. Waiting.

Trying to calm your racing pulse and swallowing thickly, you started to type.

**You X:XX PM:** Oh, yes!

 **You X:XX PM:** I mean, yes, I am free tonight.

 **You X:XX PM:** And I still want to.

You set the D.D.D. back down on the desk to wait for a response, glancing uselessly back at your work. There was no chance it was getting done now - not when you had a good idea of what was in store for your evening. You sighed, trying to calm yourself, and gathered and packed away your work. You would tend to it tomorrow, energy willing. It wasn’t long before your D.D.D. buzzed again.

**Lord Diavolo X:XX PM:** Excellent! I’ll send someone over to escort you to the castle soon!

That was that. You pursed your lips, debating if you should take anything particular with you. Would you need pajamas or the like? You weren’t sure. First, though, you needed to inform Lucifer you would be absent for the night. Surely he wouldn’t deny you if it was under Diavolo’s invitation, but it was best to be safe. Hopefully, he wouldn’t question _why_ Diavolo was calling you to the castle on such short notice.

* * *

Several hours later, after arriving at the castle and being treated to a warm welcome, followed by dinner and pleasant conversation, you found your nerves growing again. The casual questions about how things were for you at RAD and how the brothers were doing put you tentatively at ease, but the tension remained not far beneath the surface. The occasional flash of intensity in Diavolo’s eyes or the way they sometimes lingered on you longer than necessary did nothing to lessen your nerves.

Ordinarily, conversation with Lord Diavolo was a little unsettling, but pleasant, and it was plain enough that he meant well. There was no underlying tone or pre-arranged event waiting for you those other times. But now, _now_ was different. You could hardly forget the reason you had been invited that evening. At the same time as it made your pulse race with nerves, there was anticipation and excitement alongside them. You didn’t regret your decision or your choice of words at the party, but you couldn’t contain the flood of emotions either.

After dinner, you thanked Barbatos for the wonderful meal and several Little Ds that had assisted with its serving. Diavolo rose, coming to your seat and helping you to your feet. His hand smoothed over the small of your back, his touch soft. “Let’s retire to my room, shall we?” He invited warmly with a wide smile.

Your stomach twisted giddily, and you nodded, falling in step with him out of the dining room and down the lavish halls. The casual, friendly conversation continued, Diavolo pointing out paintings or displays you hadn’t seen your first time around or that had been acquired since your tour of the castle. But it was hard to pay attention with his touch on your back and his hip brushing yours as you walked.

When you finally arrived at the door to Diavolo’s chambers, your belly was in nervous knots, heart drumming wildly, and a tingling growing between your legs. The anticipation was almost a high all its own, only amplified by your nerves. You urged the anxiousness to relax, reminding yourself silently that you had made this choice. You could easily have refused in your texts, but you had gladly agreed instead.

Opening the door, Diavolo gestured for you to enter with a sweep of his other arm and you stepped into the room. He followed shortly after, the door closing behind him with a soft ‘click’. There was no sound of turning locks, which came as little surprise. Diavolo was the castle’s lord after all - any demon burst without warning into his room was asking for trouble, after all.

The room was more quaint and cozy than you had expected. A couple of sofas surrounded a circular glass table, the room lit warmly by a lantern on the wall, a candle-lined chandelier on the ceiling, and an ornate lamp on a bedside table. Several landscapes decorated the walls and just beyond the sofas waited a four-poster canopy bed, looking simple but large and plush. Overall, the room felt warm and inviting, rather than gaudy or glamorous.

Diavolo brushed past you, taking one hand carefully in his and leading you to the foot of the bed. “Tell me, do you remember what it was you said the night of the party?” He asked, golden eyes boring heatedly into yours. The intensity of it was striking, almost unsettling.

At first, you nodded mutely, pulling your lip between your teeth for a second. “I do…” you squeaked out quietly.

“And? What was it?” It was easy to tell Diavolo was being coy. If he had forgotten your words, you doubted he would have summoned you to the castle in the first place or brought you to his private quarters. He wanted you to repeat yourself.

“Don’t go easy on me, my lord,” you said, surprised by the breathiness of your speech.

“Are you sure?”

Diavolo’s face was gentle but serious. His words were warm, comforting, a last chance to denounce your words and run away. But you had already made your decision when you answered his text. Already steeled your resolve, even if your stomach writhed like it was full of butterflies.

“Yes.” Your voice was quiet, but firm, leaving no doubts to be had.

Diavolo smiled playfully and you caught a glint of something sharp and mischievous in his golden eyes.

“Let’s get started then,” he suggested, the wide smile lingering on his lips. “Oh, but first…” The air hummed with energy and shimmered, making the hair on your arms and neck stand on end, and you watched as Diavolo’s form shifted until the beautiful demon form that had so enamored you previously was facing you. “Is this what you’ve been waiting for?” He asked 

Just like that, your attempt to temper the swirling in your gut, the way you made to keep your voice steady, all of it shattered. The change in Diavolo’s form brought to mind the evening past, a veritable wave of lust crashing over you and threatening to drown you in its thick, fiery embrace. But why was the effect so nearly _overwhelming_ this time around? Even before, when Diavolo had trapped you against the wall, you hadn’t felt the hunger so strongly. Was there a component of will to the alluring aura Diavolo’s demon form cast? If he willed it so, was it stronger?

“I… yes, I could hardly forget,” Your voice fell to a hush as you stared greedily at Diavolo. No longer held back by the boundaries of what was appropriate or polite, you were free to devour the feast of flesh in front of you.

Diavolo needed no further answer, smoothly stepping closer and draping his arms around you. One swept upward, cradling the back of your skull in one large hand. His tapered nails grazed lightly against your skin. His other hand curled lower, smoothing down your spine until it rested again on the small of your back, urging your body toward him. His wings moved forward, wrapping around your shoulders and back, caging you in a leathery sheet of black and red. You hardly dared to move your head, flanked on either side by the ornately decorated tips of Diavolo’s curving horns when he dipped his head.

His lips captured yours in a kiss that oozed passion and strength and for a second you couldn’t breathe, frozen and dumbstruck. But that passed, and you leaned into the kiss, looping your arms beneath one set of his wings and crossing them over his back. A feral rumble from deep in his chest made you shiver against him, squeezing yourself even tighter to him, despite the golden jewelry on his chest digging into you.

Diavolo broke away, leaving you waiting with parted lips and desire-heated skin, intent and waiting. His eyes were half-lidded, molten gold shining down on you as he admired your face. Then he was back on you, taking advantage of the opening in your lips to thrust his tongue into your mouth. He explored your mouth hungrily as if you were the most delicious thing he had tasted in days before tangling your tongue with his and deepening the kiss.

A small muffled moan slipped through the kiss, eliciting an echoing sound from Diavolo. His hands shifted again, the motion feverish and almost impatient. Both moved past your back, curving under your ass and wrapping around the back of your thighs. Before you could react, your feet left the ground and Diavolo pulled your legs around his waist, pressing you more flush against him.

Before, fully distracted by his kiss, you had hardly registered the growing bulge through Diavolo’s pants. Yet held so tightly to him, there was no missing it. Your breathing quickened and you dug your fingers into his skin, the hot feeling of his length adding fuel to the fire. It was maddeningly arousing to have him so intimately close, separated from your core by only a few layers of flimsy cloth. A moan rolled up your throat and Diavolo bucked his hips teasingly, hoping to lure out another.

You hooked your ankles together, clinging to Diavolo as he started to grind firmly, slowly, against you, his hands moving to hold your ass in a rough. Another of the needy noises he was searching for escaped, muted and desperate. Surrounded by heat and muscle, the frantic rush of any lasting nerves died away and all you could entertain was the thought of how good it all felt.

With a soft nip at your lips, his fangs making it sting more than it otherwise might have, Diavolo pulled away from your mouth, turning his attention to your jaw and your throat. Between the fiery touch of his lips and tongue on your skin and the continuing, insistent press of him against your core, all you could register was the pleasant buzz building on your skin and in between your legs. Your head fell back, allowing Diavolo easier access, and your mouth dropped open, a series of gasps and groans slipping out into the still air.

Your sense of time dissolving, you weren’t sure how long you stayed that way, Diavolo lavishing attention on your skin and moving down inch by agonizingly slow inch until he was mouthing at the lines of your collarbone left exposed by your clothes. But eventually, you felt him move, the gentle rush of air as he made his way towards the nearby bed making a chill shoot through you.

You let him ease your legs from around his waist and he settled you onto the bed. He leaned in smoothly, putting his lips to your ear, the tip of one horn scraping your cheek. “Take those off and then lie down,” he bade you. The husky tone of his voice easily worked another shudder from you.

You obeyed as he straightened up, his golden eyes remaining locked on you. You weren’t sure the heat in your cheeks could grow any greater, but it sure felt like it as you stripped off your clothes. You swallowed thickly several times and wet your lips, a task that should have been quick and simple stalled several times by the intensity of Diavolo’s expression. Finally, you had stripped down to nothing, shuffling back on the sheets and lying back tentatively.

“There, perfect.” you heard his deep tone praise. “Now, what should I do with you?” Diavolo continued with a hum of thought. There was silence for a moment as you lay staring up at the canopy of the bed. “Mm, I know.”

The shuffling of something in a drawer beside the bed drew your attention. You glanced toward the sound, watching as Diavolo withdrew several lengths of silken ribbon, Your face flitted between confusion and curiosity, mind buzzing. Your curiosity was quickly sated when Diavolo came to your side, brandishing the length of ribbon. He pulled each arm out beside you, tying a loop of the ribbon around each wrist, before tying the other end to the columns of the bed. He repeated himself with each ankle as he rounded the end of the bed.

You weren’t sure if it was fear or anticipation - or both - that swelled in your chest once you were completely bound, naked and vulnerable with your legs spread open. Judging by the wetness gathering between your thighs though, you were willing to bet on the latter. Maybe it would have been saner to be scared in the face of being bound and helpless before a demon of such great power, but something about it was exhilarating.

You watched Diavolo as he looked over his handiwork, pausing to take in more of your body. Satisfied with your bonds, he clambered onto the bed, settling himself on his knees between your legs. His fierce, lustful gaze returned to yours, eyeing him from your position against the plush pillows. “Remember, little human, you asked for this,” he teased, moving his hands to your thighs.

The tender skin twitched reflexively under his touch, ticklish from the light trail of his nails. The pads of his fingers smoothed over them, stroking lazily, inching closer to your core. At the apex of your thighs, one hand stopped to knead the soft flesh, now and then gingerly scraping his nails over it. The other continued upward, until the tips of two fingers trailed over your soaked folds, parting them but only barely. All the while his burning eyes never left your face, carefully studying each minute change in expression.

Your breath hitched in your throat again and a soft whine left you as his fingers explored more boldly. His fingers slid past your lips, prodding at your slit, one-by-one dipping inside and pushing deeper. You whimpered, testing the bonds on your wrists and clenching your fists. He eased his fingers in and out, slowly at first, scissoring and stretching you before inserting a third. His thumb brushed against your clit and you bucked your hips reflexively. His name rolled off your tongue and you longed to dig your fingers into the sheets beside you.

“Lord Diavolo, please, please untie me,” you whined. Your torment had barely begun, yet being at his unrushed mercy was already weighing on you.

“I don’t think so. I can’t very well punish you like that, can I now?” Diavolo’s voice held a faux-seriousness, but the hungry undertones betrayed him and you made another plaintive sound. “You’ll just have to wait and take it.”

His fingers hooked, his pace slowing, becoming more searching and deliberate. When you arched your hips again and cried out, the muscles in your thighs flexing as you tried to pull at the ties around your ankles, he knew he had found what he was looking for. Despite his deliberately slow pace, the hints of orgasm were approaching swiftly, and you strove to urge it closer, arching into his touch and trying to adjust his pace. 

The tension in your gut rose steadily and you squeezed your eyes closed, biting your lip, sweat beading on your forehead lightly as the heat swelled alongside the tension. “Aaa, fuck, Diavolo,” you groaned, voice strained and breathy. “Don’t stop, oh right there feels. So. Good.”

Diavolo’s rolling chuckle met your demand, amused and husky, but he obliged you, stroking you a bit more ardently. Your moans and whimpers reached a fever pitch and you struggled against your ties again unconsciously as the first hints of release washed over you. His name left your mouth several times, mixed amongst moans. Beyond the sound of your voice and the blood rushing in your ears, you barely noted the pleased hum from Diavolo.

When your body relaxed, your cunt still fluttering with the fading burst of pleasure, Diavolo withdrew his fingers. You weakly lifted your head, just in time for a view of him bringing his soaked digits to his lips and stuffing them into his mouth. You groaned again, feeling your pussy pulse again a bit more violently in response. Diavolo cleaned his fingers slowly, savoring the sweet, tangy taste before freeing them.

“Oh, you look tired already and we’ve only just started,” he said, feigning disappointment. “That won’t do,” he added, shifting on the bed. He bent down, his head leveling with your cunt, the ridges of his gilded horns scratching at your thighs, “Cum for me again, won’t you?” His voice was soft and heavy, not quite pleading, but with a hint of mischief.

You groaned at the sensation of his hot breath on your still oversensitive cunt, once again bucking your hips instinctively. His tongue flickered out, swiping up your folds, earning a stronger taste of your essence. When he reached your clit, drawing the tip in circles over it, you arched back down into the sheets away from the overstimulation. “I-I can’t,” you whimpered, your attempts to escape Diavolo’s probing tongue failing, “Lord Diavolo, please, it’s t-too much.”

“You can and you will. You’ll need it.”

You bit down on your lip again as Diavolo continued, alternating between tracing his tongue over your swollen nub and sucking on it lightly. Beneath the pain of overstimulation grew the onset of another orgasm, making your legs quiver and your voice more airy and desperate. Your breathing picked up again, coming in short, hard puffs the closer your second orgasm crept. You made a sound that was half-yelp, half-groan when Diavolo’s fingers slid back into your pussy, reaching again for the spot inside you that would put you over the edge.

Your cries rose to a shout when you reached the peak of your second climax and crashed over the edge, once again pulling against your bindings out of reflex. You called Diavolo’s name again, interspersed with more curses and cries, your voice cracking. 

When your latest orgasm had ebbed and Diavolo drew his fingers out again, you slumped against the sheets. Thoroughly sweat-slicked and feeling hot and sore already, a couple of tears streaking down your cheeks, you were content to lie still. Though Diavolo didn’t grant you the reprieve you sought, his tongue moving down from your clit to lap greedily for a moment at your slick cunt. You whimpered pitifully in response, the overstimulation even greater than before.

When Diavolo had taken his fill, he sat back, peering down at you, amber eyes half-lidded and pupils wide with his desire. He allowed you a minute to catch your breath and some stimulation to fade, shifting his hands up for a time to grope at your tits. You groaned, the feeling a relief compared to the over sensitivity of your cunt, but enough to make your breath stall. He leaned forward, the touch of his brooch and golden chains on your skin refreshingly cool on your heated skin, ruff and horns tickling you.

“Are you ready for your proper punishment, my little human?” He whispered.

You drew your lip between your teeth again, eyes widening at the thought that he wasn’t done with you and the true punishment had yet to come. But as he had reminded you earlier, you had asked him not to go easy on you - even if you hadn’t understood what that entailed. You nodded, swallowing a new lump in your throat.

Diavolo sat back, climbing off the bed to dispose of his decorative collar and brooch, as well as stripping off his pants. As he moved back onto the bed, you couldn’t help but watch. Your heart leaped and a tinge of panic surged through you as your eyes swept down Diavolo’s toned body, finally landing on his cock. What you had felt pressed against you before and imagined paled compared to the monstrous erection Diavolo sported. Long, thick, and hard, pre-cum dribbling freely from the flushed head, a vein standing out and throbbing in time with his heartbeat.

Your mouth opened and sputtered, intending on insisting there was no way he would fit, but all that came out was nonsense. Despite the panic that had set upon you, you couldn’t deny the sight of Diavolo in all his glory aroused you as much as it scared you. Part of you wondered fleetingly if you should have taken the opportunities he had given you to escape. But there was no going back now.

Diavolo’s face was a blend of emotions. Passion and want, mixed with amusement and something almost smug - lending a sense of ‘I _warned_ you’ without saying it. He placed two fingertips to your lips as he settled over you, hushing you gently. With Diavolo stretched over you, pressed so close, you felt small, the sense of vulnerability from before resurfacing. “Relax. Breathe,” he soothed, a hand gently palming one breast, while he stroked your jaw with the back of the other.

You tried to do as he instructed, drawing a deep breath and pushing away your panic, trying to relax against the sheets. Diavolo dipped to capture your lips again, helping to distract you further for a time before breaking away again. You felt the tip of him shift against your thighs, searching for a moment before the bulbous head nudged at your entrance. You fought the urge to stiffen up as he pushed forward, his girth already stretching you.

He eased forward, slower than you had expected, though each inch felt like the punishment he had promised. With each bit of his cock that sank into you came the growing sensation that you were going to be split in two. “Fuck fuck, fuck,” you cursed in a hiss. “There’s too much, it hurts.”. 

Tears welled up in your eyes again, threatening to break away and stain your cheeks. Beneath the pain, your cunt tensed and you felt hot and horny, a backdrop to the discomfort of Diavolo’s intrusion.

“Easy,” he rumbled, again trying to comfort you, even as he eased forward further. “Don’t worry. You’re so wet it won’t take long to get used to me,” he reassured you. Both hands had moved to your breasts, rolling and teasing your nipples between the pads of his fingers, adding some pleasure to offset the pain.

Finally, when it felt like you might burst, the last of Diavolo’s cock disappeared inside you. The sensation of fullness was almost nauseating at first and peering between your bodies you could make out a bulge in your abdomen. You lay your head back fully, taking several deep breaths to adjust. Diavolo looked down patiently, still massaging your breasts and basking in the hot, soft tightness of your cunt.

Ever so slowly, he ground his hips against yours, the motion just enough to incite your pussy to clench around him from the friction, making his cock throb and twitch. Twin groans echoed from you and you tugged at your bindings. The pain was subsiding, becoming an acceptable complement to the heat in your belly, and you grew used to how completely Diavolo filled you.

The easing tension on your face and in your body wasn’t lost on Diavolo. He tentatively drew out a couple of inches before driving back home. You moaned, the noise only briefly touched with discomfort. He repeated the motion, withdrawing a bit more than before and the next sound that escaped you was only pleasure. “You’re taking me so well now,” he praised in your ear and you finally arched up against him. “What do you want, little human?” he asked smoothly with another tentative roll of his hips.

When you answered him, your words were breathy, pain replaced with need. “Move, please. Just move, fuck me, I need more,” you begged.

Your obscene plea drew a satisfied sound not unlike a growl from Diavolo and he began to move in earnest. His pace escalated steadily, his lips falling to your throat and sucking dark marks into your skin. Each cant of his hips rocked you, the bed shaking around you as well. His hands abandoned your nipples, snaking down your body until they rested on your hips, holding them to drive into you more firmly.

The stroke of his body soon had you building towards a third release, the length of his heavy cock filling and stroking every inch of your pussy in a way that had spots forming in your vision. Your cunt squeezed around Diavolo, as if hesitant to allow his cock to leave its hold.

“Can you cum for me one last time? I want to feel you,” he groaned in your ear, speech dripping with desire.

Teetering on the edge again, you answered him eagerly. “Yes, yes! Oh fuck, Lord Diavolo, yes!” you cried out.

His tempo picked up more, encouraged by your enthusiasm. “Diavolo, Diavolo, fuck, fuck, Diavolo!” you crooned, tumbling into orgasmic euphoria for the third time that evening, your cunt clenching his cock desperately as you came.

With several even stronger thrusts, Diavolo followed. With a noise partly groan and roar, he came, filling you with jets of hot, thick cum. Truly exhausted, you didn’t move, the only sounds your labored breathing and your pounding heart. Buried inside you still, you could feel the beat of Diavolo’s heart as well, the length of his body heavy and hot above you.

After a time, he pulled out, cum seeping out and dripping onto the rumpled sheets mixed with your fluids. You made no attempt to move as Diavolo got up, untying each of your limbs before climbing back onto the bed beside you. He pulled you, winded and boneless, into his embrace, trapping you comfortably against his chest. You drew a deep breath, letting out in a heavy, tired sigh, and snuggled against his skin.

“Come, let’s get you cleaned up,” he told you, rising with you tucked in his arms. “Then you can rest. But I’m not done with you either. Remember, you’re not getting off easy.”

**Author's Note:**

> I don’t usually comment on endowment specifically, but I think a lot of people headcanon Diavolo as just being large overall, plus it seemed fitting for punishment. Also this was a bit softer/gentler thing overall than I intended but I am okay with that.
> 
> If there was any part you liked in particular, don’t be afraid to let me know! If you’d like to follow me elsewhere or make a request or just chat, you can find my on tumblr or on Twitter @BijuyoAO3!
> 
> [https://bjy-on-ao3.tumblr.com](https://bjy-on-ao3.tumblr.com/)


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